Structure and absolute stereochemistry of the anticancer agent EBC-23 from the Australian rainforest.
EBC-23 (2), a prostate anticancer agent, was isolated from the fruit of Cinnamomum laubatii (family Lauraceae) in the Australian tropical rainforest. Extensive NOE experiments enabled the relative stereochemistry of the proposed EBC-23 (2) structure to be determined. Total synthesis of both enantiopodes over nine linear steps, involving challenging RCM and spiroacetal cyclizations, confirmed the gross structure and relative and absolute stereochemistry.
Dong
Lin
L
School of Molecular and Microbial Sciences, University of Queensland, Brisbane, Queensland, Australia.
Gordon
Victoria A
VA
Grange
Rebecca L
RL
Johns
Jenny
J
Parsons
Peter G
PG
Porzelle
Achim
A
Reddell
Paul
P
Schill
Heiko
H
Williams
Craig M
CM
D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry*; D001315:Australia; D027424:Cinnamomum / Q000737:chemistry; D002980:Climate; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis / Q000737:chemistry*; D011891:Rain; D013141:Spiro Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism; D014197:Trees
D000970:Antineoplastic Agents; C534557:EBC-23; D011714:Pyrans; D013141:Spiro Compounds